Chicago (ORD) to San Juan (SJU), Jan 17–20, 2027: from $280 round trip
Chicago (ORD) to San Juan (SJU), Jan 17–20, 2027: from $280 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $280 round trip, Axel-exclusive, Frontier Airlines, 1 stop, Jan 17–20, 2027, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-01-17 → 2027-01-20 | American Airlines | AA3096 / AA2436 | 08:05:00→14:48:00 4h 43m nonstop · 05:00:00→08:39:00 5h 39m nonstop | Axel-exclusive $462.25 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | United Airlines | UA695 / UA2089 | 14:16:00→21:00:00 4h 44m nonstop · 08:25:00→11:47:00 5h 22m nonstop | Axel-exclusive $483.75 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | Frontier Airlines | F93346 / F92871 + F91441 | 23:53:00→06:32:00 4h 39m nonstop · 05:19:00→12:00:00 8h 41m 1 stop via ATL | Axel-exclusive $280.25 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | DM | DM5481 + DM1002 / DM1003 + DM5420 | 05:45:00→15:03:00 7h 18m 1 stop via PUJ · 16:24:00→22:20:00 7h 56m 1 stop via PUJ | Axel-exclusive $387.00 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | Delta Air Lines | DL5666 + DL1961 / DL1780 + DL2804 | 06:00:00→16:56:00 8h 56m 1 stop via JFK · 14:55:00→22:36:00 9h 41m 1 stop via BOS | Axel-exclusive $451.50 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | American Airlines | AA1555 / AA2436 | 17:01:00→23:39:00 4h 38m nonstop · 05:00:00→08:39:00 5h 39m nonstop | Axel-exclusive $462.25 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | United Airlines | UA1996 / UA2089 | 08:52:00→15:40:00 4h 48m nonstop · 08:25:00→11:47:00 5h 22m nonstop | Axel-exclusive $483.75 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | American Airlines | AA1889 + AA2098 / AA2436 | 12:05:00→21:13:00 7h 08m 1 stop via CLT · 05:00:00→08:39:00 5h 39m nonstop | Axel-exclusive $439.25 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | Delta Air Lines | DL1687 + DL1946 / DL1780 + DL2804 | 08:04:00→17:46:00 7h 42m 1 stop via ATL · 14:55:00→22:36:00 9h 41m 1 stop via BOS | Axel-exclusive $451.50 | 2026-10-29T01:53:25Z |
| 2027-01-17 → 2027-01-20 | United Airlines | UA1128 + UA2025 / UA2089 | 13:00:00→22:22:00 7h 22m 1 stop via IAD · 08:25:00→11:47:00 5h 22m nonstop | Axel-exclusive $460.75 | 2026-10-29T01:53:25Z |
Hotels in San Juan for these trips
Hotels: under a trip, hotels in San Juan for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in San Juan for these nights (Jan 17–20, 2027 · 3 nights · 2 adults, 1 room): 3★ Decanter Hotel · 4★ The Royal Sonesta San Juan · 5★ Condado Vanderbilt Hotel
Route overview: Chicago to San Juan (SJU) flight deals
2027-01-17 → 2027-01-20 · Axel-exclusive $462.25
- American Airlines AA3096: ORD 2027-01-17 08:05:00 → SJU 2027-01-17 14:48:00; nonstop; 283 minutes. Local airport times.
- American Airlines AA2436: SJU 2027-01-20 05:00:00 → ORD 2027-01-20 08:39:00; nonstop; 339 minutes. Local airport times.
2027-01-17 → 2027-01-20 · Axel-exclusive $483.75
- United Airlines UA695: ORD 2027-01-17 14:16:00 → SJU 2027-01-17 21:00:00; nonstop; 284 minutes. Local airport times.
- United Airlines UA2089: SJU 2027-01-20 08:25:00 → ORD 2027-01-20 11:47:00; nonstop; 322 minutes. Local airport times.
2027-01-17 → 2027-01-20 · Axel-exclusive $280.25
- Frontier Airlines F93346: ORD 2027-01-17 23:53:00 → SJU 2027-01-18 06:32:00; nonstop; 279 minutes. Local airport times.
- Frontier Airlines F92871 / F91441: SJU 2027-01-20 05:19:00 → ORD 2027-01-20 12:00:00; 1 stop(s) via ATL; 521 minutes. Local airport times.
- F92871: SJU 2027-01-20 05:19:00 → ATL 2027-01-20 08:26:00; layover at ATL: 131 minutes.
- F91441: ATL 2027-01-20 10:37:00 → ORD 2027-01-20 12:00:00.
2027-01-17 → 2027-01-20 · Axel-exclusive $387.00
- DM DM5481 / DM1002: ORD 2027-01-17 05:45:00 → SJU 2027-01-17 15:03:00; 1 stop(s) via PUJ; 438 minutes. Local airport times.
- DM5481: ORD 2027-01-17 05:45:00 → PUJ 2027-01-17 12:30:00; layover at PUJ: 88 minutes.
- DM1002: PUJ 2027-01-17 13:58:00 → SJU 2027-01-17 15:03:00.
- DM DM1003 / DM5420: SJU 2027-01-20 16:24:00 → ORD 2027-01-20 22:20:00; 1 stop(s) via PUJ; 476 minutes. Local airport times.
- DM1003: SJU 2027-01-20 16:24:00 → PUJ 2027-01-20 17:25:00; layover at PUJ: 105 minutes.
- DM5420: PUJ 2027-01-20 19:10:00 → ORD 2027-01-20 22:20:00.
2027-01-17 → 2027-01-20 · Axel-exclusive $451.50
- Delta Air Lines DL5666 / DL1961: ORD 2027-01-17 06:00:00 → SJU 2027-01-17 16:56:00; 1 stop(s) via JFK; 536 minutes. Local airport times.
- DL5666: ORD 2027-01-17 06:00:00 → JFK 2027-01-17 09:20:00; layover at JFK: 170 minutes.
- DL1961: JFK 2027-01-17 12:10:00 → SJU 2027-01-17 16:56:00.
- Delta Air Lines DL1780 / DL2804: SJU 2027-01-20 14:55:00 → ORD 2027-01-20 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
- DL1780: SJU 2027-01-20 14:55:00 → BOS 2027-01-20 18:11:00; layover at BOS: 149 minutes.
- DL2804: BOS 2027-01-20 20:40:00 → ORD 2027-01-20 22:36:00.
2027-01-17 → 2027-01-20 · Axel-exclusive $462.25
- American Airlines AA1555: ORD 2027-01-17 17:01:00 → SJU 2027-01-17 23:39:00; nonstop; 278 minutes. Local airport times.
- American Airlines AA2436: SJU 2027-01-20 05:00:00 → ORD 2027-01-20 08:39:00; nonstop; 339 minutes. Local airport times.
2027-01-17 → 2027-01-20 · Axel-exclusive $483.75
- United Airlines UA1996: ORD 2027-01-17 08:52:00 → SJU 2027-01-17 15:40:00; nonstop; 288 minutes. Local airport times.
- United Airlines UA2089: SJU 2027-01-20 08:25:00 → ORD 2027-01-20 11:47:00; nonstop; 322 minutes. Local airport times.
2027-01-17 → 2027-01-20 · Axel-exclusive $439.25
- American Airlines AA1889 / AA2098: ORD 2027-01-17 12:05:00 → SJU 2027-01-17 21:13:00; 1 stop(s) via CLT; 428 minutes. Local airport times.
- AA1889: ORD 2027-01-17 12:05:00 → CLT 2027-01-17 15:10:00; layover at CLT: 85 minutes.
- AA2098: CLT 2027-01-17 16:35:00 → SJU 2027-01-17 21:13:00.
- American Airlines AA2436: SJU 2027-01-20 05:00:00 → ORD 2027-01-20 08:39:00; nonstop; 339 minutes. Local airport times.
2027-01-17 → 2027-01-20 · Axel-exclusive $451.50
- Delta Air Lines DL1687 / DL1946: ORD 2027-01-17 08:04:00 → SJU 2027-01-17 17:46:00; 1 stop(s) via ATL; 462 minutes. Local airport times.
- DL1687: ORD 2027-01-17 08:04:00 → ATL 2027-01-17 11:00:00; layover at ATL: 141 minutes.
- DL1946: ATL 2027-01-17 13:21:00 → SJU 2027-01-17 17:46:00.
- Delta Air Lines DL1780 / DL2804: SJU 2027-01-20 14:55:00 → ORD 2027-01-20 22:36:00; 1 stop(s) via BOS; 581 minutes. Local airport times.
- DL1780: SJU 2027-01-20 14:55:00 → BOS 2027-01-20 18:11:00; layover at BOS: 149 minutes.
- DL2804: BOS 2027-01-20 20:40:00 → ORD 2027-01-20 22:36:00.
2027-01-17 → 2027-01-20 · Axel-exclusive $460.75
- United Airlines UA1128 / UA2025: ORD 2027-01-17 13:00:00 → SJU 2027-01-17 22:22:00; 1 stop(s) via IAD; 442 minutes. Local airport times.
- UA1128: ORD 2027-01-17 13:00:00 → IAD 2027-01-17 16:03:00; layover at IAD: 86 minutes.
- UA2025: IAD 2027-01-17 17:29:00 → SJU 2027-01-17 22:22:00.
- United Airlines UA2089: SJU 2027-01-20 08:25:00 → ORD 2027-01-20 11:47:00; nonstop; 322 minutes. Local airport times.
Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.
Explore this route
- All dates for this route
- Jan 16, 2027 · Return options
- Jan 18, 2027 · Return options
- Hotels in San Juan with Axel
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- This page: Chicago (ORD) to San Juan (SJU) · Jan 17, 2027 · return Jan 20, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in San Juan for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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